Ethanol → (4R)-5,6-Dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine dihydroiodide

HRID 2068531ノート

反応式

HRID 2068531 の反応式
[I:1][Si](C)(C)C.[CH:6]1[N:10]2[C:11]3[CH:30]=[CH:29][CH:28]=[CH:27][C:12]=3[CH2:13][CH2:14][C@@H:15]([NH:16]C(=O)OCC3C=CC=CC=3)[C:9]2=[N:8][CH:7]=1.C(O)C.CCCCCC.C(O)C>ClCCl>[IH:1].[IH:1].[CH:6]1[N:10]2[C:11]3[CH:30]=[CH:29][CH:28]=[CH:27][C:12]=3[CH2:13][CH2:14][C@@H:15]([NH2:16])[C:9]2=[N:8][CH:7]=1

参加物

6

反応物 4

HCID 702EthanolHCID 85247Trimethylsilyl iodide2 回HCID 21879635Ethanol hexaneHCID 58304077benzyl N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamate

生成物 1

HCID 67234232(4R)-5,6-Dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine dihydroiodide収率 98.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Add iodotrimethylsilane (783 mL, 5.49 mol) to dichloromethane (800 mL) and cool in an ice water bath. Dissolve benzyl N-[(4R)-5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-yl]carbamate (610 g, 1.83 mol) in dichloromethane (1 L) and add to the iodotrimethylsilane solution. After addition is complete, remove the ice water bath and allow the reaction to stir for approximately 16 hours at ambient temperature. Stir a mixture of hexanes (6 L) and ethanol (1 L) in an ice water bath. Add the reaction mixture to the stirring hexane/ethanol mixture carefully to avoid foaming. Stir it at ambient temperature 10 minutes. Remove the resulting solid by filtration and wash the cake with hexanes (3×2 L) to give the title compound (817.1 g, 98%) as an orange, free flowing solid: MS (m/z): 200 (M+1).

後処理

  1. temperaturecool in an ice water bath
  2. additionAfter addition
  3. customremove the ice water bath
  4. customthe reaction
  5. stirringStir
  6. stirringStir it at ambient temperature 10 minutes
  7. customRemove the resulting solid
  8. filtrationby filtration
  9. washwash the cake with hexanes (3×2 L)

出典と根拠

ORDレコード
ord-b423691cad1645e99d60bd8dfb7ee8e3
出典データセット
uspto-grants-2012_10
特許番号
US08299061B2

反応ノート

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